Deals on vacations and trips to Middlebury

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Middlebury flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Sunset Dunes Vacation Villas

Sunset Dunes Vacation Villas

3 out of 5
Price was $429, price is now $373 per person
$373
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Miami (MIA) to South Bend (SBN)
This villa features laundry facilities. Take advantage of the free self parking.
Hotel O Daylight Inn Elkhart I-90, In

Hotel O Daylight Inn Elkhart I-90, In

2.5 out of 5
Price was $632, price is now $544 per person
$544
per person
Apr 16 - Apr 19
just found
Roundtrip non-stop flight included
Denver (DEN) to South Bend (SBN)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A fireplace in the lobby and laundry facilities are also provided.
La Quinta Inn & Suites by Wyndham South Bend

La Quinta Inn & Suites by Wyndham South Bend

3 out of 5
Price was $1,048, price is now $901 per person
$901
per person
Apr 16 - Apr 19
just found
Roundtrip non-stop flight included
Denver (DEN) to South Bend (SBN)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free self parking, and a free airport shuttle. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Farmstead Inn & Conference Center

Farmstead Inn & Conference Center

2.5 out of 5
Price was $628, price is now $553 per person
$553
per person
Apr 16 - Apr 19
just found
Roundtrip non-stop flight included
Denver (DEN) to South Bend (SBN)
This hotel features an indoor pool and a gym. There's fun for all ages with a children's pool and a playground, and families will appreciate the picnic area. Guests will appreciate free perks like free self parking and WiFi in public areas.
Relaxing Riverside 10 Minutes to Shipshewana

Relaxing Riverside 10 Minutes to Shipshewana

2 out of 5
Price was $839, price is now $749 per person
$749
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to South Bend (SBN)
This vacation home includes free WiFi in public areas and barbecue grills.

Top Middlebury hotels deals

Essenhaus Inn & Conference Center

Essenhaus Inn & Conference Center

3.5 out of 5
240 Hwy 20 Middlebury IN
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $122 total per night
$122 total
Mar 15 - Mar 16
Total with taxes and fees
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
Hampton Inn & Suites Middlebury

Hampton Inn & Suites Middlebury

2.5 out of 5
105 Crystal Heights Blvd Middlebury IN
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $132 total per night
$132 total
Apr 4 - Apr 5
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Enjoy the hot tub and free perks like buffet breakfast and free self parking. A 24-hour business center, free WiFi in public areas, and a snack bar/deli are also on offer.
Pool
Hot Tub
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

Middlebury IN
$135 nightly
The price is $144 total per night
$144 total
Mar 11 - Mar 12
Total with taxes and fees
A garden is available at this cottage.
Kitchen
Free WiFi
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.

Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.

Middlebury IN
Get rates
This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
Lemon Hill Amish Guest House. . . an Amish themed, whole house experience.

Lemon Hill Amish Guest House. . . an Amish themed, whole house experience.

Middlebury IN
$204 nightly
The price is $218 total per night
$218 total
Mar 15 - Mar 16
Total with taxes and fees
This farm stay features a garden, laundry facilities, and barbecue grills.
Free WiFi
Air conditioning
Van Buren Hotel

Van Buren Hotel

4 out of 5
1175 Van Buren Street Shipshewana IN
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $125 total per night
$125 total
Apr 5 - Apr 6
Total with taxes and fees
This hotel features an indoor pool and a gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A terrace, a lobby fireplace, and a computer station are also on offer.
Pool
Breakfast included
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See all available properties in Middlebury
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Ducks in lake

Stone Lake

Commune with nature and explore the great outdoors at Stone Lake during your travels in Middlebury. While in this family-friendly area, you can enjoy the restaurants.

Stone Lake
A trail on a sunny day in the Krider World’s Fair Garden in Middlebury, Indiana.

Krider Gardens

After visiting Krider Gardens, make a plan to see the other sights and activities in Middlebury. While in this family-friendly area, you can enjoy the restaurants.

Krider Gardens

Meadow Valley Golf Club

Enjoy a round of golf in Middlebury at Meadow Valley Golf Club. While in this family-friendly area, you can enjoy the restaurants.

Meadow Valley Golf Club

Frequently asked questions

How much are vacation packages to Middlebury?
With deals starting at just $373, hotel and flight packages are a superb way to stretch your travel budget. Watch out Middlebury — here you come!
How long should my Middlebury vacation be?
Most sightseers vacation in Middlebury for approximately 2 nights. That being said, travel is all about discovering hidden gems and losing yourself in the moment — why not book a few extra nights so you can do just that?
Where can I get the best vacation package deals for Middlebury?
With at least 400 airline partners and 1,000,000 properties across the globe, it's hard to top Travelocity. Browse our comprehensive range and pick up the best Middlebury package deal. Isn't it amazing when planning a trip is that easy?
Why should I book my Middlebury vacation package with Travelocity?
Travel is all about making fantastic new memories and leaving all your worries behind — which is why we provide you with a professional team of customer service experts available 24/7 should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best price available on our terrific range of vacation packages. So what are you waiting for? There's no time like the present to secure the vacation you've always dreamed of.
Will I save money on my Middlebury car rental if I combine it with hotels and flights?
With a Middlebury vacation package, you can bundle your flight, hotel and car bookings and save a whole lot. If you're eager to uncover the best of this fantastic destination, why not start with Wrigley Field? This well-known attraction is 100 mi from Middlebury. With your own wheels, you'll be there in a flash.
Which airport is best for Middlebury?
There's a very good chance you'll land at South Bend Intl. Airport (SBN), situated 30 mi west of downtown Middlebury. Fort Wayne Intl. Airport (FWA) (55 mi away from central Middlebury) and Kalamazoo-Battle Creek Intl. Airport (AZO) (40 mi away from central Middlebury) are other choices.
What is there to do in Middlebury?
Deutsch Kase Haus should be toward the top of your travel itinerary. After you've crossed off this leading attraction, simply stroll the streets of Middlebury and find out what makes this vibrant place tick.
Where should I stay when visiting Middlebury?
If you're searching for someplace comfortable to lay your head, have a look at the Hampton Inn & Suites Middlebury. It's the top choice for many travelers.

Photos of local treasures

Browse Middlebury vacation photos for more inspiration

Amish Log Cabin
Amish Log Cabin
Amish Horse and Buggy
MIDDLEBURY, INDIANA, UNITED STATES - MAY 22nd, 2018: View of amish carriage along the city, known for simple living with touch of nature contacy, plain dress, and reluctance to adopt conveniences of
Rowboat on river at Miller's Cider Mill in Amish Country in Middlebury, northern Indiana